Yeah I've used both Tail for Win32 and tail on Cygwin. I've found both to be excellent, although I prefer Cygwin slightly as I'm able to tail files over the internet efficiently without crashes (Tail for Win32 has crashed on me in some instances).
So basically, I would use tail on Cygwin and redirect the output to a file on my local machine. I would then have this file open in Vim and reload (:e) it when required.
